title: Easy access to aroma active unsaturated γ-lactones by addition of modified titanium homoenolate to aldehydes.
abstract: The homo-Reformatsky reaction, in which a metal homoenolate of an ester is added to an aldehyde, was adapted to produce γ-lactones from unsaturated, enolizable aldehydes. By use of titanium homoenolate, 11 different γ-lactones were synthesized in one step with moderate to good yields from readily available aldehydes. In particular, this procedure allowed the rapid preparation of a series of C(12) unsaturated γ-lactones differing in the position and configuration of the double bond. These reference compounds will be used to identify previously unknown lactones in butter oil. The chromatographic, spectral, and sensory descriptions of the synthesized lactones are provided.
authors.affiliation: Corporate R&D Division, Firmenich SA, Geneva, Switzerland. eric.frerot@firmenich.com
authors.forename: Eric
authors.initials: E
authors.lastname: Frerot
authors.forename: Alain
authors.initials: A
authors.lastname: Bagnoud
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002849:Chromatography, Gas; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009812:Odorants; D021241:Spectrometry, Mass, Electrospray Ionization; D014025:Titanium / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D007783:Lactones; D014025:Titanium